Dimethyl Sulfoxide → HCID 67820243, compound

HRID 2379784Notes

Reaction equation

HRID 2379784 reaction equation
[H-].[Na+].Br[CH:4]1[C:9]([CH3:11])([CH3:10])[O:8][C:7]2[CH:12]=[CH:13][C:14]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:15][C:6]=2[CH:5]1O.[NH:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].CS(C)=[O:35]>>[CH3:10][C:9]1([CH3:11])[O:8][C:7]2[CH:12]=[CH:13][C:14]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:15][C:6]=2[C@@H:5]([N:27]2[CH2:31][CH2:30][CH2:29][C:28]2=[O:32])[C@@H:4]1[OH:35]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 120252-PyrrolidoneHCID 24758Sodium hydride2×HCID 14210536HCID 14210536, compound

Product 1

HCID 67820243HCID 67820243, compound

Procedure

0.75 g (0,025 mole) of 80% NaH is introduced into 8.2 g (0.02 mole) of 3-bromo-3,4-dihydro-2,2-dimethyl-6-(4-methylphenylsulfonyl)-2H-benzo[b]pyran-4-ol in 30 ml of dimethyl sulfoxide. After stirring at 20° for one hour, a further 0.75 g (0.025 mole) of 80% NaH and 1.9 ml (0,025 mole) of 2-pyrrolidone are added, and the mixture is stirred at 40° for 45 minutes and at 20° for 6 hours. It is introduced into ice-water and then the precipitate is filtered off with suction, dried and recrystallized from methanol several times.

Workup

  1. stirringthe mixture is stirred at 40° for 45 minutes and at 20° for 6 hours
  2. filtrationthe precipitate is filtered off with suction
  3. customdried
  4. customrecrystallized from methanol several times

Sources & evidence

ORD record
ord-f789f056cbf44ea1b6df5ba202dceade
Source dataset
uspto-grants-1994_11
Patent number
US05364878

Reaction notes

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